Potassium Bromide → HCID 178421550, compound

HRID 964562Notes

Reaction equation

HRID 964562 reaction equation
[CH3:1][C:2]1[C:3]([C:19](OCC)=[O:20])=[N:4][C:5]2[C:6]=1[C:7]([CH3:18])=[C:8]1[C:16]([CH:17]=2)=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[CH:14]2)=[N:9]1.[K+].[Br-]>C(CN)O>[OH:20][CH2:19][CH2:3][NH:4][C:19]([C:3]1[C:2]([CH3:1])=[C:6]2[C:5]([N:4]=1)=[CH:17][C:16]1[C:8]([N:9]=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[C:7]2[CH3:18])=[O:20]

Participants

4

Reactant 2

HCID 253877Potassium BromideHCID 19367650HCID 19367650, compound

Product 1

HCID 178421550HCID 178421550, compound

Reagents, catalysts & solvents 1

HCID 700EthanolamineSolvent

Procedure

Ethyl 3,4-dimethylpyrrolo[3,2-b]carbazole-2-carboxylate (1.00 g, 3.26 mmol) was suspended in ethanolamine (5 ml) and heated at reflux (giving an orange solution) under nitrogen for 1.5 hours, by which time TLC showed no remaining starting material. The excess ethanolamine was removed in vacuo and the yellow residue was triturated with DCM. The resulting solid was recrystallised from ethanol/water to give the product (two crops combined) (0.383 g, 36.5%) with m.p. 270° C. (decomp.). δH [2 H6 ]-DMSO 10.90 (1H, br s, 1-NH), 10.59 (1H, s, 5-NH), 8.09 (1H, d, J 9, 9-H), 7.89 (1H, t, J 5, amide NH), 7.85 (1H, s, 10-H), 7.29-7.45 (2H, m, 6-H, 7-H), 7.08 (1H, t, J 7.5, 8-H), 4.80 (1H, t, J 5,O-H) 3.60 (2H, quartet, J 6, 2'-CH2), 3.23-3.50 (2H, m, 1'-CH2), 2.92 and 2.86 (2×3H, 2×s, 3-CH3 and 4-CH3); m/z (%) 321 (87, M+), 303 (72), 260 (100), 231 (64), 69 (67); νmax (KBr disc)/cm-1 3334, 1587, 1543, 1309, 1250.

Workup

  1. temperatureheated
  2. temperatureat reflux (
  3. customgiving an orange solution) under nitrogen for 1.5 hours
  4. customThe excess ethanolamine was removed in vacuo
  5. customthe yellow residue was triturated with DCM
  6. customThe resulting solid was recrystallised from ethanol/water
  7. customto give the product (two crops combined) (0.383 g, 36.5%) with m.p. 270° C. (decomp.)

Sources & evidence

ORD record
ord-92de5b2b7b794b0a9d41dbcc29e2e135
Source dataset
uspto-grants-1998_06
Patent number
US05770598

Reaction notes

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